2-(benzothien-3-yl)ethylacetamide | 23962-25-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(benzothien-3-yl)ethylacetamide
• 英文别名: N-Acetyl-3-benzothienyl-aethylamin；N-(2-benzo[b]thiophen-3-yl-ethyl)-acetamide；N-(2-Benzo[b]thiophen-3-yl-aethyl)-acetamid；2-(Benzo[b]thien-3-yl)ethyl acetamide；3-(2-Acetylaminoethyl)benzo[b]thiophene；N-[2-(1-benzothiophen-3-yl)ethyl]acetamide
• CAS: 23962-25-6
• 化学式: C₁₂H₁₃NOS
• mdl: MFCD24390995
• 分子量: 219.307
• InChiKey: VECDRHALXOLWFK-UHFFFAOYSA-N

物化性质

• 熔点：
  68 °C
• 沸点：
  452.4±28.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzothien-3-yl)ethylacetamide 在 盐酸 、 硼烷四氢呋喃络合物 、 硫酸 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 32.0h， 生成 3-Ethyl-5-phenyl-1,2,3,4,5-pentahydroazepino[4,5-b]benzothiophene
  参考文献：
  名称：

  Modified Ibogaine Fragments:  Synthesis and Preliminary Pharmacological Characterization of 3-Ethyl-5-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]benzothiophenes

  摘要：

  Five phenyl-substituted derivatives and analogues of 1,2,3,4,5,6-hexahydroazepino[4,5-b]indol 5, a major fragment of ibogaine (1), were synthesized and tested for binding to monoamine transporters, the NMDA receptor-coupled cation channel, and dopamine and opioid receptors. All five derivatives, 9 and 17a-d, displayed 8-10-fold higher affinity at the DA transporter than ibogaine and noribogaine (4). At the serotonin transporter,: two compounds (9 and 17a) exhibited higher potency than ibogaine, while the rest had weaker binding affinities than the lead compound. In keeping with their structural similarity to ibogaine, all five compounds displayed weak to poor affinity for dopamine D1 and D2 receptors. However, two compounds, 17a,c, demonstrated moderate binding affinities at dopamine D3 receptors. All five compounds displayed weak to poor affinities for mu and kappa opioid receptors and for the NMDA receptor-coupled cation channel. Despite the qualitative differences, derivatives and analogues of 5 may serve as useful substitutes for ibogaine.

  DOI：

  10.1021/jm980156y
• 作为产物：
  描述：

  苯并[b]噻吩-3-乙腈 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 2-(benzothien-3-yl)ethylacetamide
  参考文献：
  名称：

  Modified Ibogaine Fragments:  Synthesis and Preliminary Pharmacological Characterization of 3-Ethyl-5-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]benzothiophenes

  摘要：

  Five phenyl-substituted derivatives and analogues of 1,2,3,4,5,6-hexahydroazepino[4,5-b]indol 5, a major fragment of ibogaine (1), were synthesized and tested for binding to monoamine transporters, the NMDA receptor-coupled cation channel, and dopamine and opioid receptors. All five derivatives, 9 and 17a-d, displayed 8-10-fold higher affinity at the DA transporter than ibogaine and noribogaine (4). At the serotonin transporter,: two compounds (9 and 17a) exhibited higher potency than ibogaine, while the rest had weaker binding affinities than the lead compound. In keeping with their structural similarity to ibogaine, all five compounds displayed weak to poor affinity for dopamine D1 and D2 receptors. However, two compounds, 17a,c, demonstrated moderate binding affinities at dopamine D3 receptors. All five compounds displayed weak to poor affinities for mu and kappa opioid receptors and for the NMDA receptor-coupled cation channel. Despite the qualitative differences, derivatives and analogues of 5 may serve as useful substitutes for ibogaine.

  DOI：

  10.1021/jm980156y

文献信息

• Bioactive tricyclic ibogaine analogs
  申请人：Regents of the University of Minnesota

  公开号：US05616575A1

  公开（公告）日：1997-04-01

  Ibogaine analogs are provided, which are phenyl-substituted-hexahydroazepino[4,5-b]indoles useful to treat cocaine addiction and the use of other addictive substances.

  提供伊波甲因类似物，这些是苯基取代的六氢吲哚[4,5-b]环己胺，可用于治疗可卡因成瘾和其他成瘾物质的使用。
• Some derivatives of [1]benzothieno[2,3-c]pyridine and [1]benzothieno[3,2-c]pyridine
  作者：K. Clarke、C. G. Hughes、A. J. Humphries、R. M. Scrowston

  DOI：10.1039/j39700001013

  日期：——

  4-dihydro[1]benzothieno[2,3-c]pyridine derivatives (I) have been prepared by Bischler–Napieralski cyclisation of the N-acetyl or N-benzoyl derivative of the appropriate 2-(5-substituted 3-benzo[b]thienyl) ethylamine. Attempts to prepare 3,4-dihydro-1-(3,4-dimethoxybenzyl)[1]benzothieno[2,3-c] pyridine and its 6-chloro-analogue by a similar method gave the 1-(3,4-dimethoxybenzoyl) derivative in each case

  1,6-二取代的3,4-二氢[1]苯并噻吩并[2,3- c ]吡啶衍生物（I）是通过Bischler-Napieralski环化适当的2-（-）的N-乙酰基或N-苯甲酰基衍生物制备的5-取代的3-苯并[ b ]噻吩基）乙胺。尝试制备3,4-二氢-1-（3,4-二甲氧基苄基）[1]苯并噻吩并[2,3- c通过类似的方法，通过吡啶和其6-氯类似物，分别得到1-（3,4-二甲氧基苯甲酰基）衍生物。用硼氢化钠将3,4-二氢衍生物（I）还原为相应的1,2,3,4-四氢衍生物（II），并用钯制木炭将其脱氢为完全芳族化合物（III）。也可以通过适当的2-（5-取代的3-苯并[ b ]噻吩基）乙胺与乙醛或苯甲醛的Pictet-Spengler反应制备四氢化合物（II）。
• Substituted pyrazoles as p38 kinase inhibitors
  申请人：Naraian S. Ashok

  公开号：US20070078146A1

  公开（公告）日：2007-04-05

  A class of pyrazole derivatives is described for use in treating p38 kinase medicated disorders. Compounds of particular interest are defined by Formula IA wherein R 1 , R 2 , R 3 and R 4 are as described in the specification.

  描述了一类吡唑衍生物，用于治疗p38激酶介导的疾病。特别感兴趣的化合物由公式IA定义，其中R1、R2、R3和R4如规范中所述。
• Compounds For the Inhibition of Undesired Cell Proliferation and Use Thereof
  申请人：Knolle Jochen

  公开号：US20080194524A1

  公开（公告）日：2008-08-14

  The present invention is related to compounds having formula (I) wherein the dashed line indicates a single or double bond or is absent and wherein A 1 -A 9 , Q, R 1 -R 11 , T, U, V, W 1 -W 3 , X 1 , X 2 , Y and Z are as defined in the claims and description, pharmaceutical compositions comprising the compounds and the use of the compounds for the manufacture of a medicament for the treatment of diseases involving abnormal cell proliferation, undesired cell proliferation, abnormal mitosis and/or undesired mitosis.

  本发明涉及具有式（I）的化合物，其中虚线表示单键或双键或不存在，A1-A9，Q，R1-R11，T，U，V，W1-W3，X1，X2，Y和Z如权利要求和说明书所定义，包括该化合物的制药组合物和用于制造治疗涉及异常细胞增殖、不良细胞增殖、异常有丝分裂和/或不良有丝分裂疾病药物的化合物的用途。
• Sulfur Analogs of β-Carbolines
  作者：Werner Herz

  DOI：10.1021/ja01167a047

  日期：1950.11